Hydrochloric Acid → 1-Hydroxy-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentane

HRID 377301ノート

反応式

HRID 377301 の反応式
[C:1]1([C:7]2[N:8]=[CH:9][O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=1)[CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][C:30]1=[O:34].Cl>O1CCCC1.C(OCC)(=O)C>[OH:34][C:30]1([C:9]2[O:10][C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH2:31][CH2:32][CH2:33][CH:29]1[CH2:28][C:27]1[CH:35]=[CH:36][CH:37]=[C:25]([O:24][CH3:23])[CH:26]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6134984,5-DiphenyloxazoleHCID 114242592-(3-Methoxybenzyl)cyclopentanoneHCID 178418339Butyllithium

生成物 1

HCID 193585111-Hydroxy-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentane

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4,5-diphenyloxazole in tetrahydrofuran (100 ml) at -78° C. under nitrogen was added n-butyllithium (in hexane, 1,7N, 12 ml). After 30 minutes, at the same temperature a solution of 2-(3-methoxybenzyl)cyclopentanone (3.8 g) in tetrahydrofuran (10 ml) was added dropwise thereto. After being stirred for 1 hour at 0° C., the reaction mixture was poured into a mixture of ethyl acetate (200 ml) and 1N-hydrochloric acid (50 ml). The organic layer was washed with saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed (n-hexane--ethyl acetate:5:1-2:1) on silica gel to afford 1-hydroxy-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentane (8.0 g).

後処理

  1. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe oily residue was chromatographed (n-hexane--ethyl acetate:5:1-2:1) on silica gel

出典と根拠

ORDレコード
ord-ba5a9907b0fd41f2aa07702cd82f2860
出典データセット
uspto-grants-2000_02
特許番号
US06025375

反応ノート

読み込み中…